It’s one of those images that feels like it was taken yesterday, even though it’s been nearly four decades. November 17, 1987. Aberdeen Airport, Scotland. A Royal Air Force plane touches down on a blustery, grey afternoon, and out steps the most famous woman on Earth: Princess Diana, 26 years old, wind whipping her honey-blonde hair into a halo of chaos, cheeks flushed, eyes sparkling with that trademark mischief. She’s wearing the ultimate anti-protocol outfit: an oversized cream cable-knit jumper (rumoured to be borrowed from her bodyguard), a flowing tartan skirt that catches the gale like a sail, and flat brown boots. No hat. No gloves. No stiff formality. Just pure, unfiltered Diana: regal yet relaxed, glamorous yet grounded, the People’s Princess in her absolute prime.

And then come the boys.

Trailing just behind her, holding her hands, are two tiny princes who look like they’ve been dressed by the same cheeky stylist who decided rules were for breaking. Prince William, five years old and already sporting that future-king seriousness, and Prince Harry, three and a half, cheeks round as apples, both in identical outfits: little red coats with brass buttons, grey shorts, knee-high socks, and polished brown shoes. Matching berets tilted at the exact same angle. The only difference? William’s slightly protective grip on his little brother and Harry’s unmistakable “I’m about to bolt” grin.

The wind hits them the second they step onto the tarmac. Diana’s skirt billows, her jumper flaps, the boys’ berets threaten mutiny, and in that glorious, unguarded moment, the photographer’s shutter captures magic. Click. History freezes. The photo explodes across front pages the next morning with headlines screaming “Diana the Dazzler!” and “The Windswept Princess and Her Little Soldiers!” It becomes, instantly, one of the most iconic royal images of the 20th century, reprinted a million times, framed in dorm rooms, tattooed on arms, cried over in documentaries.

But why does this single frame, taken on a random Tuesday in Aberdeen, still stop us dead in 2025?

The Day the Monarchy Let Its Hair Down (Literally)

This wasn’t supposed to be a photo op. The trio were en route to a private weekend on the Balmoral estate, and protocol normally dictated stiff coats, hats, and zero wind exposure. But Diana, as always, rewrote the script. She reportedly laughed when aides tried to hand her a headscarf: “Darlings, it’s Scotland, not Ascot. Let the wind have its fun.” She wanted the boys to feel the wild Scottish air, not be trussed up like museum pieces. The matching outfits? Her idea too, a playful nod to military tradition but executed with the warmth of a mum who just thought her sons looked adorable in miniature uniforms.

The result was revolutionary. For the first time, the public saw the royal family not as porcelain dolls behind palace gates, but as a real, windswept, laughing mum with two little boys who were clearly having the time of their lives. Diana’s relaxed posture, the way she crouched slightly to keep the boys steady against the gusts, the sheer joy radiating from all three of them, it shattered the fourth wall. This wasn’t duty. This was delight.

The Hidden Heartbreak Behind the Smile

Look closer, though, and the photo carries the faint shadow of what was to come. Ten years later, almost to the day, Diana would be gone. William would be 15, Harry 12, walking behind her coffin in a moment that scarred a generation. The little boys clutching their mother’s hands in 1987 had no idea that this carefree airport dash would become one of the last truly innocent snapshots of their childhood.

Royal photographer Anwar Hussein, who took the original shot, later said: “I remember thinking, ‘This is what happiness looks like.’ She was so alive that day. The wind made her glow. And the boys… they worshipped her. You could see it in every frame.”

38 Years Later: The Photo That Refuses to Age

Fast-forward to November 17, 2025, exactly 38 years later, and the image is everywhere again. William and Harry are grown men, fathers themselves, estranged in ways no one could have predicted that windy afternoon. Yet the photo trends yearly on this date like clockwork.

Fashion houses have tried (and failed) to recreate the oversized cream knit. Tartan skirts are flying off racks every November. And every year, someone starts a petition to erect a statue of Diana in exactly this pose: wind in her hair, sons at her side, smiling like the world could never hurt them.

The Eternal Message in the Wind

In the end, that’s why the photo endures. It’s not about the clothes, the matching berets, or even the future king and his spare holding mummy’s hands. It’s about a young mother who, for one blustery afternoon in 1987, let the wind mess up her hair and decided that joy mattered more than protocol.

Thirty-eight years on, on another cold November day, we’re still chasing that feeling.

Diana didn’t just emerge from a plane that afternoon. She emerged as the blueprint for what royalty could be: warm, real, and gloriously, defiantly human.

And somewhere, if you listen closely when the wind picks up, you can almost hear her laughing.